C-LINKED GLYCOSYL AZIDO ACID IN NOVEL SOLID-PHASE C-GLYCOPEPTIDE SYNTHESIS

A C-linked glycosyl decapeptide was synthesised on solid-phase by a co mbination of the Fmoc-method and a novel method of using azido acids w ith reductive deprotection. The unprotected C-glycosyl azido acid buil ding block was incorparated by a TBTU coupling, subsequently reduced u sing DTT in DMF and followed by further Fmoc-amino acid-OPfp ester cou plings. Mouse hemoglobin (67-76) carrying the C-linked glycoside in po sition 72 was prepared as a metabolically stable T-cell glycopeptide a ntigen. (C) 1998 Elsevier Science Ltd. All rights reserved.